Inside Billy Crystal and Late Rob Reiner's Friendship Over the Years

Billy Crystaland Rob Reinermay have started out as costars - but their working relationship soon blossomed into a five-decade friendship.

In 1975, Crystal was cast as Rainer's friend Al Bender in All in the Family.

"I hadn't met Rob before, and here we were cast as best friends," Crystal recalled in a guest column for The Hollywood Reporter titled "Billy Crystal: How Rob Reiner and I Built a Bromance of Four Decades" in September 2016. "What impressed me the most about Rob was, one, he was so genial, but two, he was so smart … It's a very impressive combination of talents that I first met - plus, he was just hilarious."

Reiner cast Crystal in small roles in 1984's This Is Spinal Tap and 1987's The Princess Bride before choosing him to star in the 1989 hit When Harry Met Sally alongside Meg Ryan.

"Whenever you do something this personal and you're best friends, if it doesn't work, it's like, ‘Oy!'" Reiner told Peoplein a 2019 interview on casting Crystal in the film. "Finally, I said, ‘Aw, f*** it; he's perfect!'"

The twosome continued to show up for each other throughout the years at various premieres, including at the premiere of Reiner's Spinal Tap II: The End Continues in September 2025.

In December 2025, Rob and Michele Reiner were found dead in their Los Angeles home. He was 78 years old.

Keep scrolling to learn more about Crystal and Rob's decades-long friendship:

1975

After making brief appearances in This Is Spinal Tap and The Princess Bride, Rob cast Crystal in the lead role of Harry Burns opposite Meg Ryan in When Harry Met Sally.

Although Rob considered other actors such as Albert Brooks, Tom Hanks and Michael Keaton for the part of Harry, he decided Crystal was "the best one."

"Not only did [Crystal] nail it, but he contributed like crazy," Rob shared on The Howard Stern Show in 2016.

Rob noted that "whenever you do something this personal and you're best friends, if it doesn't work, it's like, ‘Oy!'"

"Finally, I said, ‘Aw f*** it; he's perfect!" Rob told People in 2019."The biggest laugh in any film I've ever done was a line Billy came up with: ‘I'll have what she's having.'"

One of Crystal's favorite memories with Rob happened at the first screening of When Harry Met Sally.

"Rob and I were sitting in the back next to each other. Then the orgasm scene happens, and the place goes berserk," Crystal recalled to The Hollywood Reporter in 2016. "When Rob's mother, Estelle, says, ‘I'll have what she's having,' it was thunderous, a laugh you can only hear with the best of jokes in a concert hall. It's those moments that make movies so spectacular. … We just grabbed each other's hands because we knew something exciting was about to happen with this movie."

2021

Crystal supported Rob at the premiere of his film Spinal Tap II: The End Continues.

December 2025

On December 14, TMZ reported that the Los Angeles Fire Department had been called to Rob and his wife Michele's house to administer "medical aid." The outlet reported that a 78-year-old man and 68-year-old woman had been killed in the home with a spokesperson for the family later confirming that the victims were both Rob and Michele.

"It is with profound sorrow that we announce the tragic passing of Michele and Rob Reiner," a statement shared with Variety read. "We are heartbroken by this sudden loss, and we ask for privacy during this unbelievably difficult time."

Billy and his wife, Janice Crystal, were seen walking down the street near Rob's home following the deaths, per footage obtained by ABC 7. A neighbor told the outlet that Billy "looked like he was about to cry."

The following day, Us Weekly confirmed that Rob and Michele's 32-year-old son, Nick Reiner, had been arrested on a murder charge following their deaths. (Rob and Michelle shared kids Nick, Jake and Romy with Michelle. He also shared daughter Tracy with ex-wife Penny Marshall.)

US Weekly

This story was originally published December 16, 2025 at 11:37 AM.